Discover Carlisle, NY: The Upstate Small Town Spilling Revolutionary Tea
Explore the Route 20 town where patriots built the Great Chain, bluebirds found their way home, and small-town kindness still greets every traveler.
Population: 1,502 Square miles: 34.1 Median age: 46.5 Per capita income: $45,144
By the books, the Town of Carlisle, on the northernmost edge of Schoharie County, may seem like the typical small town in upstate New York with “rolling hills, spectacular views, working landscapes, tranquil communities, and deep history.”
Carlisle’s main road? Route 20. Spanning 3,365 miles coast-to-coast, it’s the longest highway in the United States — and with 372 of those miles crossing New York from Massachusetts to Pennsylvania, it’s the state’s longest too. Postcard worthy? Yes. Quietly luring road-trippers, wanderers, and history buffs off the beaten path? Yes. Is there revolutionary local lore waiting to be spilled?
Also yes.
JD Lehew and Rocky Kinzer (Team Long Road) climb Route 20 out of Carlisle.
In June 2022, retired Marines JD Lehew and Rocky Kinzer (Team Long Road) passed through Carlisle on foot during their 3,000-mile journey from Delaware to the Pacific. Their mission: a revolutionary act of remembrance honoring the 81,600+ U.S. service members still MIA since WWII.
No big ceremonies awaited them here. Instead, simple acts of kindness — a wave from a porch, a bottle of water at the gas station, a quiet “thank you” from strangers who understood.
“Those hills, they’re killers,” joked JD as they climbed past old barns, weathered stone walls, and the graves of local Revolutionary War heroes. What stayed with them most wasn’t the challenge, but the connection—the way Carlisle made them feel seen, even without a grand welcome.
Just north of Route 20, Carlisle Cemetery, the final resting place of two extraordinary patriots:
Thomas Machin, a Carlisle native, who famously tossed tea into Boston Harbor, fought at Bunker Hill, and in 1778 engineered The Great Chain—a massive iron barrier across the Hudson River that stopped British naval advances north.
Judge John Brown, a captain in the American Revolution at Battle of Cobleskill (1778) and at Lower Fort (now Old Stone Fort Museum) when the British burned the valley in a violent raid, one of Schoharie County’s first judges (1795), and author of the county’s first written history.
Like to explore old cemeteries? Carlisle’s Revolutionary War heroes Thomas Machine and Judge John Brown are buried beside these markers.
The Tea on Carlisle
Carlisle was officially formed on March 31, 1807, carved from the neighboring towns of Cobleskill and Sharon. Two centuries later, in 2007, the Carlisle Historical Society celebrated its bicentennial by publishing a whopping 350-page tome, History of the Town of Carlisle: Schoharie County, New York Bicentennial Edition, 1807–2007. Today, the town’s story lives on in its historic hamlets: Rock District (home to the first schoolhouse and mill), Carlisle Center, Grovenors Corners, and Argusville.
Beneath Carlisle’s rolling hills lies a hidden world—literally. The town is home to McFail’s Cave, the longest cave system in the Northeast at more than seven miles underground, along with dozens of other caves like Cave Mistake, Cave Disappointment, and Ice Cave. Just down the road and more widely known, Howe Caverns (caves discovered by a cow) and Secret Caverns.
Legend has it Lieutenant Peter Young hid his crippled wife in the small cave known as Rock House while rushing the rest of his family to the Old Stone Fort during the Battle of Cobleskill.
Local lore tells of Lieutenant Peter Young, who hid his wife in a cave now known as Rock House during a British-backed raid on Schoharie County—the breadbasket of the American Revolution. Oh the stories these caves could tell…
Above ground, a treasured legacy of conservation including the famous New York State Bluebird Trail. Thanks to Carlisle native Ray Briggs’ efforts in the 1990s, over 1,200 bluebird nest boxes were installed along Route 20, helping to revive New York’s threatened state bird. Unfortunately, with the passing of Briggs in 2011, many have fallen into disrepair: anyone looking for a project?
Also home to Barrack Zourie — the mountain that looks like a barrack — and reminds Schoharie County residents on I-88, “You’re nearly home, hang tight!”
Just off Route 20, dairy farms and farmstands.
Hot Tea
Carlisle (with neighboring Seward) is going green with the new state-approved Rock District Solar project—sparking community conversations about about farmland, water, and keeping the killer views. Carlisle may not headline the news but it leaves an impression on you.
It’s a place where you can walk a 3,000-mile marathon for a cause, explore centuries-old caves, restore bluebird trails, and write the next chapter of a town’s 200-year story. Whether you’re a veteran passing through, a remote worker craving quiet, or a family longing for space to breathe and grow, Carlisle offers something rare: a community that welcomes you in, even when you weren’t looking.
A small town with a welcome that echoes through the ages. Cowork with us for a day (for free) and see for yourself.
Root Access is your guide to life, work, and community in Schoharie County. Have any hot local tea? Comment below!
